Defining Moments from 27 Awesome Bloggers

The source of inspiration for this post comes from two places. The first is my own reflection on my life and what brought me to where I am today. When I was a distraught 18-year old I would have never in a million years thought I’d of volunteered in Vanuatu, backpacked South America, or run a successful location independent business for 8-years and I know that this is just the beginning of my extraordinary journey. In reflection, I realized that I went through a series of defining moments that brought me to today, just 37 days before I head out on a remarkable journey around the world for an indefinite period of time.

The first defining moment is when I went in my dad’s place (he had to have back surgery) on a cruise through the Caribbean where I met Miles. I came from a soul less Plano, TX where people were dull, lifeless, and only cared about what you wore, what you drove, and how much money was in your bank account. Miles was different. He radiated a contagious happiness that I had never before seen in my life. I couldn’t help but smile when I was around him. Miles decided that the path he was supposed to be on wasn’t what he wanted so he got his SCUBA teaching certification, packed his bags, and moved to the Caribbean to do what he loved, SCUBA diving. Miles planted a seed in me that day. I had never felt happiness like Miles radiated and I knew I wanted to do the same. But I didn’t know how.

The Caribbean changed me. I realized there was so much more out there in the world beyond Plano, TX and I was hungry for more. But I was stuck in a prison cell created by my parents to live a traditional life. One day when I was browsing the internet, daydreaming of those days in the Caribbean I stumbled across a travel blog and learned of around the world backpacking. Well, Hell. If he can do it, so can I… But I had medical bills to take care of, an apartment to pay for, a dog, and whole bunch of stuff to take care of. For a few years, I had to take care of myself and my medical needs. Those years, they fucking sucked. I hated life. I knew what I wanted.

Trapped in the castle of San Felipe – Cartagena, Colombia

Eventually, I had enough. Was I going to let my 20s be the worst years of my life when they were supposed to be the best? Isn’t there more to life than being miserable? I wasn’t going to let outside influences dictate my life and I took action on my defining moments and turned them into the fulfilling life I lead today.

The second source of inspiration for this post is all the people who tell me, “I would love to do what you do, but (enter excuse)” “I can’t leave my stable job” or my personal favorite, “You’re so lucky!” As if luck had anything to do with making an conscious choice. I would be in the same miserable life I was before if I didn’t give a big, “EFF YOU” to the traditional unfulfilling way of living and start living life on my terms. That “eef you?” It came with a price tag! A huge one. I sacrificed what relationship I had left with my parents, my boyfriend, my dogs, my apartment, and pretty much everything I owned. I never said it was going to be easy.

The difference from a miserable life and a remarkable one? Taking action when you have those defining moments. Not brushing them aside but saying, “enough’s, enough” and getting the hell out. Doing what it takes to get the job done in the process!

We all have defining moments and they are all different for each and every one of us. The difference between me and cubical nation? I listened, I learned, and I took action. It’s what you choose to do with those powerful defining moments that makes the difference between the mundane and the extraordinary. Here are 27 defining moments from some truly awesome people. They took these very moments and propelled themselves into the lives they lead today.

“Our lives a series of defining moments, strung together by passing time. Surrender fully to this moment, because it is not the moment itself that defines us, but how we choose to live in it.” – Jill Pendley

“I realized that I’d never be happy sitting at a desk, so I stopped. I quit. I left. Then I started a simple experiment: how can I live without money? Oh! Get rid of my stuff and don’t buy anything, easy! It’s so easy to not have a job if you realize that every single thing you own is created by an artificial desire. You’ve been conned into buying stuff by a corporation that owns you. Opt out, stop it, if you’re buying stuff at the mall you’re an idiot.”

“The reality is that it only takes a choice to be free. Make the right choice.”

“A lot of different things came together to push me to want to live in Asia for at least a year and travel abroad, but on a grander scale, my tipping point was probably just looking at the people around me in my job. Folks who’d been doing basically the same thing for 25 or 30 years, stagnating, making a living but beaten into complacency on the inside, not living life to the fullest, and not going anywhere. I just decided I didn’t want to settle for mediocre and wake up one day in 30 years to find myself in the same place, doing the same thing.”

“A little over five years ago, I realized my life was upside down — I was spending most of my time doing the things I liked least, and the least amount of my time on what was most important to me (my family and my writing). I couldn’t make it to my kids’ soccer games or be home in time to spend some time with my wife and kids. It was depressing. I decided to make some changes. A year later, I got to where I wanted to be — leading a simple, happy life.”

“I was involved in two destructive relationships. One with myself and because of that one with someone else. I was living in London on a working holiday visa. I had destroyed so many friendships with people I had once loved so much and my life was spiraling out of control. No matter what I did I couldn’t do it right and I couldn’t make things better. And then one day I woke up and knew something had to change or my life would have a very short expiration date. I made the decision that I would no longer allow my life to be like this. I realized that I had created my circumstances and that meant I could easily create a different one. So I packed up all I owned and moved to Dublin. I didn’t have any money, a job or any friends and I crawled into my hostel bed heavy with loneliness and sadness. I didn’t want to get up ever again. And then from nowhere something inside of me told me to get up, go outside and make a difference. So I did and I have never looked back. Since then my life has knowingly been of my design and it is full of joy and peace- I know that it is only me who can create this.”

“My moment came when I finally got my dream job, after years of working my way up, only to wonder, “now what?”. The sacrifices I had made in my 20s: long work hours, longer commutes, frequent business travel — had slowly become a lifestyle choice — and one that I wasn’t very happy with. Because I had reached my career goal, it felt like the perfect moment to put that part of my life aside and to try something different.”

“You know, I’d say it’s a combination of two things: One–growing up having nothing. It instilled in me a great sense of determination, and while I don’t adhere to the standard definitions of success anymore, my determination has served me in that now, whenever I decide to do something, I move forward with confidence. I’ve done food stamps. I’ve been homeless. I’m actually an orphan. I’ve had many loved ones pass. And knowing I can still prosper through those conditions? Hell, I can do anything.”

“There’s a lot of back story that went into reaching my ‘Eureka!’ moment, but the short version is that I realized the goal I’d been pursuing wasn’t what I really wanted out of life, and that unless I changed course I would reach my goal and be unhappy with it. After that realization, and working up the cajones to change my entire life around (it wasn’t easy, but the alternatives seemed much worse) I was able to move forward with as much tenacity and gusto as I had previously, just in a different direction.”

“The dissatisfaction with my job built up over three years. Throughout that time I was always able to defuse the internal tension by focuses on the good aspects of the job. But I could feel my youth slipping away. Ultimately I switched positions within the company and it was a worse fit for me. One night at the bar, I decided I needed to face these niggling doubts and tunnel my way out. I simply followed the light of my passions.”

“I’d always been entrepreneurial, but the tipping point came when one too many teachers told me “this will look good on your resume.” I decided right then, at age 19, I would never have a resume or live like a drone. And I’ve kept my promise to myself.”

“I don’t think there was one defining moment for me, but I’d say the whole experience of living in West Africa for four years cumulatively helped to give me a broader worldview and led me to what I’m doing now. I’m very grateful for those times.”

Jet Set Citizen – John Bardos is a textbook example of the new rich (experiences not money), by living, working, and playing anywhere in the world he wants to. My favorite post on his site is, “Why I am so Successful.”

“The defining moment for me was when I left Canada to move to Japan. I was procrastinating with my life and not really accomplishing anything so I finally just bought a plane ticket and left for Japan one week later. I didn’t have a job or visa and I only had about $1000 to my name, but I went anyway. It was scary as hell arriving in a foreign country without speaking the language and not knowing what to do. However, everything fell into place. I had a friend teaching English in Japan but I only had his address. I just showed up one day and asked if I could stay there. I stayed with him for a week then was introduced to someone else and then someone else. I worked many illegal jobs before securing a legitimate teaching job and a work visa. Everything just fell into place. Two years later I got married and started my own English school.”

“In February 2010, my wife and I gave up everything to reinvent our lives again. Sure it is scary to give up security for the unknown, but life is short. The time to live is now.”

“The realization one day that we could continue what we were doing (living/working in Prague) for many, many years without even noticing life slipping away. We enjoyed the security and comfort of our existence we had worked hard to build (we had arrived in Prague five years prior without jobs), but we wanted to see the world and didn’t want to wake up in 10 years and wonder, ‘what if?'”

Location Independent – Lea and JonathanWoodward quit the rat race in 2007 after getting bored of the mundane and wondering if there was more to life. They’ve become the resident experts in location independence and have created a plethora of products to help others in their journey.

“I’m not sure there was one, single, defining moment – it was more a combination and sequence of events that ultimately resulted in us making the big leap to become location independent and nomadic. It started with my Mum dying, then travelling around Australia and New Zealand for 3 months on sabbatical (getting married in Sydney along the way), quitting my job on the first day back after my sabbatical, then a complete career change and moving out of the city (of London). Those were just some of the events which laid the basic foundations for the major change of location independence! And then along the way, there continues to be a variety of defining moments which ultimately influence where we’re going and what our future plans actually become.”

“I’m not sure if there was one defining moment. There have been a lot of experiences I’ve had the culminated into me choosing to lead the life I live. But probably one of the biggest was deciding that I was going to create a business from a blog and quit my day job. That took a lot of guts for me, and I’m glad I did it.”

“One of the main turning points for me was when I studied Economics in the Czech Republic. Being away from home and my normal environment allowed me to realize many things about myself and the world. When I came back to the states, I realized that my main responsibility was to myself and my happiness. That I had the power to decide how I wanted to live, and not just follow a predetermined road map. I decided that I would unlearn everything society gave me. If it was not my experience, I would only accept it hypothetically. I then began to treat life as one huge learning experiment, an adventure.”

The Life Thing – Jonny Gibaud quit his well paid project management job to pursue a life of adventure. You can get a peek into what kind of a life Jonny has by checking out what a day or month is like.

“I was working as a Project Manager for a Swiss engineering company called Sulzer. The pay was great, good travel and an interesting vocation…I had a good life. Then a very close family member died and I remembered a favourite phrase of mine, “To have the great, you have to give up the good”. I wanted a great life and so that is what I did, I gave up the good and took a gamble on the great. I quit my job, set up a company and headed off around the world.”

“I wish I could say there was one tipping point. But it was a combination of things over a number of years that led me to this moment. At one point, I was in a job I hated, lived in a huge apartment overflowing with stuff, and didn’t have enough time to spend with the people I loved. Making changes in all of those areas took time and patience. With that being said, I’ve been inspired by a number of people to make these changes, including the Small House Society, Chris Guillebeau, and Dee Williams.”

“I’d hit it again because that shot was a defining moment, and when a defining moment comes along, you define the moment… or the moment defines you.” – Roy McAvoy

“The tipping point for me was when a job I had treated me completely like shit. I had put up with it for over four years, but one particular situation made me ask “what the hell am I doing with my life working in a place like this?”

Nomadic Matt – Matt Kepnes is a 20-something vagabond who went outside his comfort zone, quit his job, and left for a 1-year backpacking trip. However, that one year turned into four and he’s yet to settle down.

“When I went to Thailand, I met some backpackers who were traveling for months at a time. I got jealous so I came home, quit my job, and started backpacking. It was that, that lead to this.”

Location 180 – Sean Ogle spent two years crunching numbers as an analyst for an investment firm. It was the thought of being chained to a desk that made him quit his job and begin the pursuit of completing his bucket list.

“In February of 2009 I took a trip down to Rio for Carnival with one of my best friends. I was walking down Copacabana Beach on a Wednesday morning thinking that I should have the freedom to do this anytime I wanted. At the time, I couldn’t even go out and get my oil changed during a weekday if I wanted to. It was at that moment, I knew I needed to start working towards a change. I came back and within a month had started what would become Location 180.”

“The tipping point for me was when I realized that the life I was striving for and living was not my life at all. The American dream was not my dream. I don’t think there is any thing wrong with that lifestyle, it’s just not right for me. When I finally recognized that, my life started to shift in a better direction, my actions started to align with my true values.”

“Without a doubt, the birth of our daughter Milligan. Bringing her home from the hospital enabled Courtney and me – for the first time – to really reflect on where our life was and where we wanted it to be.”

“It was in those first few days that we made the life-changing decision to pay off our consumer debt, sell everything we owned, and spend a year traveling abroad. The process of taking control of our finances – and our clutter – changed us down to the very core. Traveling abroad with Milligan blew open the flood gates.”

“6 Months after I finished business school I found a job. In a moment of desperation, even though I knew it wasn’t that job I wanted, I took it. Two weeks into it I was so miserable that I decided in the span of 24 hours to quit that job. Considering I had been unemployed for 6 months, it was a big risk. I’ll be eternally grateful for having the guts to walk away. Today I love my life and have a job that I look forward to every single day.”

“Getting done with college and going ‘crap, what’s next’ – I did a lot of soul searching, worked at some bars and realized that this was not what I wanted with my life. I wanted 100% freedom, or as close as I could get so I chose entrepreneurship.”

“When I stand before God at the end of my life, I would hope that I would not have a single bit of talent left, and could say, “I used everything you gave me.” – Erma Bombeck

Raam Dev – Raam quit his job and sold all of his possessions in his transition to a minimalist, nomadic lifestyle. Without any travel experience he spent 6-months living like a nomad and traveling through three countries, on a total budget of $3,000.

“I was sitting at my desk in an office building with a good view of the Boston skyline when a bird flew past my window. It flew back and forth as if trying to get my attention before soaring off into the horizon. I stopped working for a moment and watched. It was so free, so filled with potential to explore.”

“It was then that I felt something inside me breathing its last breath. All my longing for adventure and exploration, all my passion for nomadic travel and discovery, it was all ready to give up hope. Suddenly the thought of living the rest of my life unfulfilled scared me to death. Doing nothing became more scary than risking everything. That evening I wrote an email to my boss telling him I needed to talk about my employment.”

Twenty-Something Travel – Steph has never been an enthusiast of working 9-5 for 40-years so she’s breaking out of that mold by going on an around the world backpacking trip. She recently quit her job and is writing a new love story in China.

“I think the tipping point for me was when I broke up with my boyfriend Junior year of college.We’d been together a very long time and I’d felt pretty limited in my choices. Breaking up gave me the freedom to go study abroad, where I realized how much I loved traveling. I’ve been going ever since.”

I’ve now briefly introduced you 27 amazing people and their lifes defining moments. Now you can see what built your favorite bloggers into who they are today and how they are no different from you. The only difference is what they did with those moments!

What is your moment? And more importantly, what are you doing with it? Please join in the conversation and leave a comment below.

Next Monday these very same bloggers will help you overcome the fear of the unknown giving you the kick you need to make change! Live life to the fullest! Don’t want to miss it? Be sure to subscribe to e-mail updates!

If you are looking for holiday homes in Italy be sure to check out Ferienhaus Italien.

It’s amazing what fleeting youth can do to a person. Look in the mirror enough times at 3am and you’ll realize you’re headed straight for the grave unless you take a detour!

http://www.whereisjenny.com Jenny

Right? This is me taking a detour! I’m sure I’ll redefine myself a few times over. Where are you headed?

http://www.baconismagic.ca Ayngelina

Who said the 20s were your best years? I’m assuming someone in their 20s because 30s kick ass.

Anonymous

Hell yeah, the 30’s rock

http://www.whereisjenny.com Jenny

A lot of people say the 20s are your best years. Mostly people who did nothing in their life and the 20s are when they didn’t give a damn, got drunk, went to college, and did a bunch of stupid stuff before getting, “responsible.”

I’m on my last year of my 20’s… and I think life is just beginning.

http://www.adventurebimbling.com/ Andrew Murray

A great list of travel bloggers, I enjoy most of these blogs and will certainly be investigating the others

http://www.whereisjenny.com Jenny

Right on. Glad I could introduce you to a few new peeps!

Anonymous

hey Jenny,

Thanks for including me in your post. As I said in our email exchanges I think you’re off to a great start and something tells me you’re going to be very successful in all your endeavors. In fact I was writing about you this morning in my post on how to build a tribe :). I’m learning quite a bit from watching how you are going about things.

Whoa! A great round up, Jenny. Very inspiring and encouraging read. Looking forward to the next one.

http://www.whereisjenny.com Jenny

Thanks! Glad you enjoyed it.

Anonymous

Hey Jenny, thanks for including me. I am honored to be among such awesome people.

http://www.whereisjenny.com Jenny

Pfff… You’re pretty awesome. 😉

http://twitter.com/chrisguillebeau chrisguillebeau

27 bloggers! Now here’s a *real* roundup post. Nice.

http://www.whereisjenny.com Jenny

It wasn’t supposed to be quite that many, but it happens. ; )

http://www.breakawaybackpacker.com Jaime

Wow this is a great post with so many positive defining moments. I love the my defining moment was also at the lowest moment in my life.

http://www.whereisjenny.com Jenny

Even though your DWI was your lowest moment, you’ve created a better life because of it. Had it not of happened you be spiraling down the road of mediocrity.

http://www.ourlifeinc.com Our Life Inc

WOW! This was such a fantastic post! So inspiring…my wife and I recently decided to “Live the Life You’ve Imagined”. Funnily enough, I am living the life I imagined (standard American Dream) while at the same time not living the life I imagined at all (chained up in a cubicle)!! Every decision we make now is made based on a single criteria…is this moving us closer to freedom?

At some point though…we have to jump. I am afraid and excited that the point of no return is coming faster than we think.

Thanks again…great post!

http://www.whereisjenny.com Jenny

Kudos to you for making the decision to live the life you’ve dreamed of.

Go ahead and jump, you’ll find out… it’s not as bad as it seems. In fact, it’s better.

http://www.thetravellerworldguide.com @_thetraveller_

Jenny this is amazing! So many inspirational people involved! It is really interesting to read about defining moments… they can be quite different for everyone.

http://www.whereisjenny.com Jenny

I enjoyed putting it togeather! What are yours?

http://www.traveling-savage.com Keith Savage

Awesome and inspiring list. Thanks for including me!

http://www.whereisjenny.com Jenny

Thanks for being part of it!

http://twitter.com/OneGiantStep OneGiantStep

Some excellent new people to follow! Thanks Jenny!

http://www.whereisjenny.com Jenny

Right on!

http://www.thelifething.com Jonny

Thanks for including me in this list Jen.

http://www.shesnext.com Hana Kamm

This was an excellent post. Very motivational.

http://www.GoSeeWrite.com/ Michael Hodson

great list of bloggers — thanks

http://www.heroicdestiny.com David Crandall

Love it! And I think there must be something magical about the number 27; that’s how many people I listed when I did my blogger round up not that long ago. Hmm…let’s see, it IS 3 to the 3rd power, maybe it’s the magic of 3. ;)While I’ve heard of most of the people on this list, I’m happy to see that there are a few that I was not aware of. Will definitely check them out. 😀

http://www.whereisjenny.com Jenny

Awesome. It was a lot, but that’s just kinda what happened. Glad I could introduce you to a few new ones, I tried to get a mixture of bloggers from all sizes and areas.

http://twitter.com/carmenbolanos Carmen Bolanos

Excellent list, Jenny. I see a lot of my favorites and some new ones as well. You know, choosing an alternative lifestyle like location independence means going against the norms of the larger whole. Most of the people on this list have done that. When you make that choice, there are bound to be tough times and “defining moments”. For me, that makes some of the best reading.

http://www.whereisjenny.com Jenny

Carmen, what makes this group of people so great is they said, eff it and found their true calling. They went for it and I’m hoping that other people see that they can do it too.

http://twitter.com/lachlancotter Lachlan Cotter

This is very inspirational to me. Thanks so much, Jenny!

http://www.whereisjenny.com Jenny

Awesome!! Glad you enjoyed it.

Joel

Great post and great list of blogs, Jenny! While I’ve always wanted to travel, I think my defining moment was when I lived out of a suitcase for 3 weeks for work and realized I didn’t miss ANYTHING I had back at home. It was a tremendous revelation.

http://www.whereisjenny.com Jenny

Right! Your surprised by what you didn’t even miss, but you stress out on before you leave!!

Anonymous

Great post and great list of blogs, Jenny! While I’ve always wanted to travel, I think my defining moment was when I lived out of a suitcase for 3 weeks for work and realized I didn’t miss ANYTHING I had back at home. It was a tremendous revelation.

http://twitter.com/IvanCampuzano Ivan Campuzano

thanks so much for including me with this awesome bunch :)…hope all is well…

http://www.whereisjenny.com Jenny

thanks Ivan

John Bardos

Awesome post Jenny! You are doing everything right: Amazingly comprehensive roundup post, networking with popular bloggers and a beautifully designed blog. Congratulations. I hope all your hard work really pays off for you.

http://www.whereisjenny.com Jenny

Thanks John!

http://www.artofbackpacking.com Michael

Awesome list of bloggers. I follow nearly all of them as well.
I’d say my defining moment was when a stack of bills came to my new apartment with a no window cubicle at my 9-5 job – even when I received a raise, it did nothing. It wasn’t for me so I made a change.

http://www.whereisjenny.com Jenny

Glad you made the change. Very few actually do.

http://www.MyBeautifulAdventures.com/ GlobalButterfly

There are just no words to describe how freaking inspirational this post is. Every person should read this period.

Great to hear more about the background and motivations of you and the others you profiled. I’ve read a lot posts and tweets from some of them, but didn’t know much of their personal stories. Very interesting and inspirational!

http://holesinmysoles.blogspot.com/ Jim

A good list of great bloggers I’ll add to my ‘Follows’.
Defining moment…. when a sandal maker tapped me on the forehead in tsunami wrecked India, and blessed me. Kind of the first thought that springs to mind.

Love this post! Will be bookmarking it and coming back to it when I need inspiration! Thanks!

http://twitter.com/Technomadia Technomadia

Fantastic round up of some of my favorite people! And I love your take on the defining moment.. has given me pause to consider what mine were. Very inspiring, thank you for bringing them all together! – Cherie

http://bayareamija.wordpress.com/ asalvesen

Wow, Jenny! What a great blog post.
It’s one thing to know that it takes more than luck to be a successful location-independent blogger – to know that it entails brave decisions made during defining moments – moments that entail sacrifice and facing your fears. But it’s another thing to actually see all of these quotes lined up one after the other. It’s very powerful.

I LOVE this article and all the insights. Everyone has the same and different stories: the common undeniable urge to live their dream and the courage to do it and the completely personal trips, lessons, and experiences.

Found your post preparing a wedding ceremony. Thanks for your inspiration. I used some of your quotes in the ceremony (I did give you credit for saying them).

Wendy

While many of these people have interesting things to say and I read several of these blogs, I’m always floored by the self-centered worldview. I don’t use “self-centered” in a pejorative sense necessarily; people can make their own choices and I’m not against “following your dreams”, certainly. But I never understand why these people don’t look for fulfillment in other ways. They talk a big game about how they do this stuff because freedom is so important, but what I seldom see people discuss is whether what it’s really all about is getting to play all their lives and being absolved of responsibility. Again, not necessarily anything wrong with that, but I wish people would own it. This kind of blogger always seems to me to act like there are two choices in life: corporate servitude or location independence. Many, many people in the US live minimalist lives, stay out of debt (in the first place, but that doesn’t make a good headline), have “escaped” meaningless corporate 9-5 jobs. And instead of traveling non-stop they find fulfillment in careers that make a real difference, like the medical field, teaching, social services. How many bloggers have tried careers like these before “chucking it all” to do something that seems like more fun? I’m not against more fun; I’m against not claiming that as a primary motivation.

http://www.ivblogger.com/ Shaeyi

Jenny, you rock and i am happy to read this article The people you listed here are great guys and gals who I am also learning from. I decided to stop working on my blog to learn all i could learn from you guys out there who has done well for the blogging industry. Keep growing big

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Who Is Jenny

Jenny is rebooting her life. She is leaving everything behind to backpack the world as a digital nomad. She doesn't know when, where, or if she's coming home.

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